CN102603720A - 9-ethyl carbazole chalcone derivative containing coumarin skeleton and synthetic method thereof - Google Patents
9-ethyl carbazole chalcone derivative containing coumarin skeleton and synthetic method thereof Download PDFInfo
- Publication number
- CN102603720A CN102603720A CN2012100499646A CN201210049964A CN102603720A CN 102603720 A CN102603720 A CN 102603720A CN 2012100499646 A CN2012100499646 A CN 2012100499646A CN 201210049964 A CN201210049964 A CN 201210049964A CN 102603720 A CN102603720 A CN 102603720A
- Authority
- CN
- China
- Prior art keywords
- ethyl
- tonka bean
- bean camphor
- chalcone derivative
- derivative
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- LVWXQYQYUUHSJX-UHFFFAOYSA-N CC[n](c1ccc(CCC(C2=Cc3c(cccc4)c4ccc3OC2=O)=O)cc1c1c2)c1ccc2Br Chemical compound CC[n](c1ccc(CCC(C2=Cc3c(cccc4)c4ccc3OC2=O)=O)cc1c1c2)c1ccc2Br LVWXQYQYUUHSJX-UHFFFAOYSA-N 0.000 description 1
- NTCCNERMXRIPTR-UHFFFAOYSA-N Oc1c(C=O)c(cccc2)c2cc1 Chemical compound Oc1c(C=O)c(cccc2)c2cc1 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 description 1
Images
Landscapes
- Indole Compounds (AREA)
Abstract
The invention discloses a 9-ethyl carbazole chalcone derivative containing a coumarin skeleton. The derivative has a structure shown as a formula I. A preparation method of the derivative comprises the following steps of: mixing a 9-ethyl-3-formoxyl carbazole derivative with a 3-acetocoumarin derivative; adding a solvent for dissolving; adding an alkaline catalyst; and heating and refluxing for 4-6 hours to obtain the derivative. The 9-ethyl carbazole chalcone derivative containing the coumarin skeleton has high stability, and the thermal decomposition temperature is over 300 DEG C; and the 9-ethyl carbazole chalcone derivative containing a coumarin skeleton shows high ultraviolet absorbance and fluorescence emission performance, and has particularly high fluorescence intensity on solid powder. Different substitution groups are introduced onto six loci, so that a luminous color changes. The synthesis and separation methods of the 9-ethyl carbazole chalcone derivative containing the coumarin skeleton are simple, and raw material sources are convenient and readily-available.
Description
Technical field
The invention belongs to the luminous organic material field, be specifically related to a kind of 9-ethyl carbazole class chalcone derivative and compound method and application that contains the tonka bean camphor skeleton.
Background technology
Carbazole is the rigid plane biphenyl structural; Having the advantages that to be prone to modification, wide energy gap, high photoelectricity stability and high-luminous-efficiency, is superior hole mobile material and blue electroluminescent material, and 3 on the carbazole structure; Go up easy binding functional group for 6, form the carbazole derivative of various uses.Carbazole arrives widely in organic electro-optic device and uses.In addition, serve as that D-π-A or the A-π-D-π-A system that the basis forms receives much concern because of having good two-photon absorption with 9-ethyl carbazole chromophoric group.
Equally; Tonka bean camphor also is to be considered to have multiple bioactive one type of important organic cpds for a long time; Extensively be present in natural product and the synthetic drugs; Add that they make them in a lot of fields at unique optical physics and spectrochemical property, like white dyes, fluorescent probe, electroluminescent, aspects such as two-photon absorption are with a wide range of applications.
(Yi-Feng Sun such as Sun Yifeng; Yi-Ping Cui.The synthesis; Characterization and properties of coumarin-based chromophores containing a chalcone moiety [J] .Dyes and Pigments; 78 (2008): 65-76.) reported a kind of tonka bean camphor cinnamophenone D-π-A system, as electron acceptor, connected electron donors such as anthracene, carbazole, triphenylamine through the π key with tonka bean camphor; Find that this system has good two photon absorption cross section; Yet,, almost do not appear in the newspapers in aspect researchs such as optical physics and spectrochemical properties for 6 chalcone derivatives of introducing electron withdrawing group and electron withdrawing group formation D-π-A system at the 9-ethyl carbazole.
Summary of the invention
For the shortcoming and deficiency that overcomes prior art; Primary and foremost purpose of the present invention is to provide a kind of 9-ethyl carbazole class chalcone derivative that contains the tonka bean camphor skeleton; This verivate has good thermostability, uv-absorbing and fluorescent emission performance, can be used as luminescent material and uses.
Another object of the present invention is to provide the above-mentioned compound method that contains the 9-ethyl carbazole class chalcone derivative of tonka bean camphor skeleton.
A purpose more of the present invention is to provide the above-mentioned purposes that contains the 9-ethyl carbazole class chalcone derivative of tonka bean camphor skeleton.
The object of the invention is realized through following technical proposals:
A kind of 9-ethyl carbazole class chalcone derivative that contains the tonka bean camphor skeleton has suc as formula the structure shown in the I:
Wherein, R is-NO
2Or-Br, R
1For-H ,-OCH
3,-OH ,-N (CH
2CH
3)
2Or-C (CH
3)
3, R
2=R
3=H or
The above-mentioned compound method that contains the 9-ethyl carbazole class chalcone derivative of tonka bean camphor skeleton may further comprise the steps:
With the 9-ethyl shown in the formula II-3-formyl radical carbazole derivative and the 3-acetocoumarin verivate shown in the formula III with mol ratio 1: (1-1.2) mix, add dissolution with solvents again, add basic catalyst then, reflux 4-6 hour; Product naturally cooling after-filtration is got deposition, will precipitate recrystallization, obtains the 9-ethyl carbazole class chalcone derivative that contains the tonka bean camphor skeleton of formula I, and following reaction takes place this process:
In formula I-III, R is-NO
2Or-Br, R
1For-H ,-OCH
3,-OH ,-N (CH
2CH
3)
2Or-C (CH
3)
3, R
2=R
3=H or
Described solvent is an absolute ethyl alcohol; Or be absolute ethyl alcohol/acetonitrile mixed solvent, wherein the volume of absolute ethyl alcohol and acetonitrile is 2: 1;
Described basic catalyst is hexahydropyridine or pyridine;
Described recrystallization adopts absolute ethyl alcohol-N mixing solutions, and both volume ratios are 2: 1;
The above-mentioned 9-ethyl carbazole class chalcone derivative that contains the tonka bean camphor skeleton can be used as luminescent material and is used to make luminescent device.
The present invention has following advantage and effect with respect to prior art:
1, the synthetic and separation method of the 9-ethyl carbazole class chalcone derivative that contains the tonka bean camphor skeleton of the present invention is simple, and raw material sources conveniently are easy to get.
2, its good stability of 9-ethyl carbazole class chalcone derivative that contains the tonka bean camphor skeleton of the present invention, heat decomposition temperature reaches more than 300 ℃.
3, the 9-ethyl carbazole class chalcone derivative that the contains the tonka bean camphor skeleton of the present invention fluorescence intensity that shows good uv-absorbing and fluorescent emission performance, particularly pressed powder is strong.Go up for 6 and introduce different substituting groups, glow color changes.
Description of drawings
Fig. 1 is that the embodiment of the invention 1 product 3-((E)-3-(3-bromo-9-ethyl-6-carbazyl) acryl) tonka bean camphor is at CH
2Cl
2In ultraviolet absorpting spectrum.
Fig. 2 is that the embodiment of the invention 1 product 3-((E)-3-(3-bromo-9-ethyl-6-carbazyl) acryl) tonka bean camphor is at CH
2Cl
2In the fluorescent emission collection of illustrative plates.
Fig. 3 is the embodiment of the invention 1 product 3-((E)-3-(3-bromo-9-ethyl-6-carbazyl) acryl) the aerial thermogravimetric analysis of tonka bean camphor (TG) graphic representation.
Fig. 4 is the fluorescent emission collection of illustrative plates of 3-((E)-3-(9-ethyl-6-carbazyl) acryl) tonka bean camphor.
Fig. 5 is 3-((E)-3-(9-ethyl-6-carbazyl) acryl) the aerial thermogravimetric analysis of tonka bean camphor (TG) graphic representation.
Embodiment
Below in conjunction with embodiment and accompanying drawing the present invention is described in further detail, but embodiment of the present invention is not limited thereto.
Embodiment 1
3-[(E)-3-(3-bromo-9-ethyl-6-carbazyl) acryl] tonka bean camphor synthetic may further comprise the steps:
(1) 9-ethyl-3-formyl radical carbazole is synthetic
At 0 ℃, N
2Protection under, 2.7mL exsiccant DMF slowly is added drop-wise to fills 4.5mL (49.6mmol) POCl
3With 2.7mL CCl
4In the round-bottomed flask of mixed solution, after dropwising, stir 10min, be warmed up to room temperature, will be dissolved with 1 of 0.5052g (2.5mmol) 9-ethyl carbazole again, 2-ethylene dichloride 10mL slowly splashes in the mixed solution.Then temperature is risen to 90 ℃, reaction 48h, thin-layer chromatography monitoring to reaction finishes.Treat its cooling, in the NaOH aqueous solution with reaction mixture impouring 50mL 5%.With ethyl acetate extraction 3 times, organic phase is used anhydrous magnesium sulfate drying, concentrating under reduced pressure with deionized water wash 2 times (100mL * 2).Liquid concentrator is through column chromatography for separation, and the petroleum ether-ethyl acetate wash-out with 10: 1 obtains white straight product, productive rate 89.3%, m.p.82～84 ℃.
Following reaction takes place in said process:
(2) 9-ethyl-3-formyl radical-6-bromine carbazole is synthetic
Take by weighing heating for dissolving in the dry benzene of N-bromosuccinimide (NBS) 0.356g (2mmol) and 3-formyl radical-9-ethyl carbazole 0.231g (1mmol) 20mL; Slowly be added drop-wise in the reaction solution with 3mL benzene dissolving 0.0243g (0.1mmol) Lucidol (BPO); Dropwise back backflow 3h; Reaction finishes, and cooling is filtered.Concentrate and to obtain thick product, get the pearl straight product, productive rate 95%, m.p.124～126 ℃ with the absolute ethyl alcohol recrystallization.
Following reaction takes place in said process:
(3) 3-ethanoyl tonka bean camphor is synthetic
Salicylic aldehyde 2.44g (20mmol) and methyl aceto acetate 2.32g (20mmol) are mixed to join in the there-necked flask, with the dissolving of 20mL anhydrous ethanol solvent, in ice-water bath, stir then; Add 1.0mL (10mmol) hexahydropyridine again and make catalyzer, ice-water bath stirring reaction 5 hours, suction filtration; With the thick product of deionized water wash; Use the absolute ethyl alcohol recrystallization then, obtain the light yellow solid product, productive rate about 87.2%; M.p.122～123 ℃.
The structural characterization data of product are: FT-IR (KBr) v:3030,2930,1936,1740,1679,1611,1558cm
-1 1H NMR (400MHz, CDCl
3/ TMS) δ: 2.74 (s, 3H), 7.32～7.40 (m, 4H), 8.52 (s, 1H).The deducibility product is a 3-ethanoyl tonka bean camphor.
(4) 3-((E)-3-(3-bromo-9-ethyl-6-carbazyl) acryl) tonka bean camphor is synthetic
Take by weighing 3-formyl radical-6-bromine carbazole 0.602g (2mmol) and 3-ethanoyl tonka bean camphor 0.376g (2mmol) in the round-bottomed flask of 50mL, add the absolute ethyl alcohol of 15mL and the hexahydropyridine of 0.5mL, reflux 4h is cooled to room temperature, and deposition is separated out.Filter, get thick product.Using volume ratio is that 2: 1 absolute ethyl alcohol-DMF mixing solutions recrystallizations get solid 0.802g, productive rate 85%, m.p.262-264 ℃.
The structural characterization data of product are:
1H NMR (400MHz, DMSO-d
6) δ: 8.68 (d, J=10.8Hz, 2H), 8.47 (s, 1H), 7.97-7.91 (m, 3H), 7.78-7.70 (m, 3H); 7.66-7.61 (m, 2H), 7.52 (d, J=8.4Hz, 1H), 7.45 (t, J=8.8Hz, 1H), 4.475 (q; J=6.4Hz, 2H), 1.32 (t, J=6.8Hz, 3H) .IR (KBr) v:3065,2967,1711,1607,1580; 1563,1473,1445,1380,1267,1229,1163,1053,987cm
-1.ESI-MS m/z (%): 967 ([2M+Na]
+, 100).Infer that product structure is as follows:
Synthesizing of 2-((E)-3-(3-bromo-9-ethyl-6-carbazyl) acryl)-benzo [f] tonka bean camphor, may further comprise the steps:
(1) 9-ethyl-3-formyl radical carbazole is synthetic
With embodiment 1 step (1);
(2) 9-ethyl-3-formyl radical-6-bromine carbazole is synthetic
With embodiment 1 step (2);
(3) 3-ethanoyl-5,6-benzene is synthetic for tonka bean camphor
With 2-hydroxyl-1-naphthaldehyde
(1.72g; 10mmol) (1.3g 10mmol) is mixed to join in the there-necked flask, dissolves with the 15mL anhydrous ethanol solvent then with methyl aceto acetate; In ice-water bath, stir; Add 0.5mL (5mmol) hexahydropyridine again and make catalyzer, ice-water bath stirring reaction 6 hours, suction filtration; With deionized water and the thick product of washing with alcohol; Use absolute ethyl alcohol and acetone recrystallization then, get the light yellow solid product, productive rate is about 76%; M.p.189～190 ℃.
The characterization data of product is following:
1H NMR (400MHz, CDCl
3/ TMS) δ: 2.81 (s, 3H), 7.51 (d, J=9.0Hz, 1H), 7.64 (t, J=8.0Hz, 1H), 7.78 (t, J=8.2Hz, 1H), 7.97 (d, J=7.9Hz, 1H), 8.13 (d, J=9.0Hz, 1H), 8.41 (d, J=8.4Hz, 1H), 9.36 (s, 1H).Infer that product structure is as follows:
(4) 2-((E)-3-(3-bromo-9-ethyl-6-carbazyl) acryl)-benzo [f] tonka bean camphor is synthetic
Take by weighing 3-formyl radical-6-bromine carbazole 0.602g (2mmol) and 3-ethanoyl benzo tonka bean camphor 0.476g (2mmol) in the round-bottomed flask of 50mL; Add the absolute ethyl alcohol of 10mL and the acetonitrile of 5mL, slowly drip the hexahydropyridine of 0.5mL again, reflux 6h; Be cooled to room temperature, deposition is separated out.Filter, get thick product.The use volume ratio is that absolute ethyl alcohol-DMF mixing solutions recrystallization of 2: 1 gets solid 0.846g, productive rate 81%, m.p.268-270 ℃.
The structural characterization data of product are:
1H NMR (400MHz, DMSO-d
6) δ: 9.32 (s, 1H), 8.67-8.65 (m, 2H), 8.44 (s, 1H), 8.31 (d, J=9.2Hz, 1H); 8.08 (d, J=8.4Hz, 1H), 7.97-7.90 (m, 2H), 7.79-7.72 (m, 2H), 7.72-7.57 (m, 5H); 4.44 (q, J=8.0Hz, 2H), 1.29 (t, J=6.8Hz, 3H) .IR (KBr) v:3060,2967,1722,1654; 1577,1481,1445,1385,1344,1229,1174,1064,973cm
-1.ESI-MS m/z (%): 1067 ([2M+Na]
+, 100). the structure of inferring product according to above information is as follows:
Embodiment 3
3-((E)-3-(9-ethyl-3-nitro-6-carbazyl) acryl) tonka bean camphor synthetic may further comprise the steps: (1) 9-ethyl-3-formyl radical carbazole synthetic
With embodiment 1 step (1);
(2) 9-ethyl-3-formyl radical-6-nitro carbazole is synthetic
Take by weighing 3-formyl radical-9-ethyl carbazole 0.231g (1mmol) and in the acetic acid of 5mL, dissolve, to the concentrated nitric acid 0.5mL (10mol) that wherein drips 65%, 20min dropwises; Stirring at room 2h; There is yellow flocks to generate, filters, extremely neutral with deionized water wash.Get yellow product 0.262g, productive rate 98%.
Following reaction takes place in said process:
(3) 3-ethanoyl tonka bean camphor is synthetic
With embodiment 1 step (3);
(4) 3-((E)-3-(9-ethyl-3-nitro-6-carbazyl) acryl) tonka bean camphor is synthetic
Take by weighing 3-formyl radical-6-bromine carbazole 0.536g (2mmol) and 3-ethanoyl tonka bean camphor 0.376g (2mmol) in the round-bottomed flask of 50mL; Add the absolute ethyl alcohol of 10mL and the acetonitrile of 5mL, slowly drip the hexahydropyridine of 0.5mL again, reflux 6h; Be cooled to room temperature, deposition is separated out.Filter, get thick product.Using volume ratio is that 2: 1 absolute ethyl alcohol-DMF mixing solutions recrystallizations get solid, and Yield 55%; M.p.278-280 ℃.
The structural characterization data of product are:
1H NMR (400MHz, DMSO-d
6) δ: 9.25 (s, 1H), 8.91 (s, 1H), 8.67 (s, 1H), 8.38 (d, J=8.8Hz, 1H), 8.00-7.93 (m; 3H), 7.87-7.82 (m, 2H), 7.79-7.71 (m, 2H), 7.52 (d, J=8.4Hz, 1H), 7.45 (t, J=7.2Hz; 1H), 4.57 (q, J=6.8Hz, 2H), 1.37 (t, J=6.8Hz, 3H) .IR (KBr) v:3054,2967,1717,1659; 1602,1569,1511,1484,1390,1327,1229,1176,1091,971cm
-1.ESI-MS m/z (%): 899 ([2M+Na]
+, 100). infer that according to above information product structure is as follows:
Product 3-((E)-3-(the 3-bromo-9-ethyl-6-carbazyl) acryl) tonka bean camphor of embodiment 1 is dissolved in the dichloromethane solution, and concentration is 1 * 10
-6Mol L
-1, measuring its uv-absorbing, the result is as shown in Figure 1, and the wavelength of its maximum absorbance correspondence is at visible region.
Embodiment 5
In product 3-((E)-3-(3-bromo-9-ethyl-6-carbazyl) acryl) the tonka bean camphor dissolving dichloromethane solution with embodiment 1, concentration is 1 * 10
-6Mol L
-1, measuring its fluorescent emission, the result is as shown in Figure 2, and compound has stronger fluorescence property, the jaundice green glow.
It is bigger that the product of embodiment 1-3 and the collection of illustrative plates (Fig. 4) of known compound 3-((E)-3-(9-ethyl-6-carbazyl) acryl) tonka bean camphor are compared fluorescence intensity.
Airborne 3-((E)-3-(3-bromo-9-ethyl-6-carbazyl) acryl) tonka bean camphor is carried out thermogravimetric analysis (TG), and the result is as shown in Figure 3, and the heat decomposition temperature of compound is 322 ℃, shows good thermostability.
The decomposition temperature of known compound 3-((E)-3-(9-ethyl-6-carbazyl) acryl) tonka bean camphor only is 300 ℃ (Fig. 5), is improved so introduce its thermostability of compound (product of embodiment 1-3) of new group.
The foregoing description is a preferred implementation of the present invention; But embodiment of the present invention is not restricted to the described embodiments; Other any do not deviate from change, the modification done under spirit of the present invention and the principle, substitutes, combination, simplify; All should be the substitute mode of equivalence, be included within protection scope of the present invention.
Claims (6)
1. 9-ethyl carbazole class chalcone derivative that contains the tonka bean camphor skeleton is characterized in that: have suc as formula the structure shown in the I:
Wherein, R is-NO
2Or-Br, R
1For-H ,-OCH
3,-OH ,-N (CH
2CH
3)
2Or-C (CH
3)
3, R
2=R
3=H or
2. the described compound method that contains the 9-ethyl carbazole class chalcone derivative of tonka bean camphor skeleton of claim 1 is characterized in that may further comprise the steps:
With the 9-ethyl shown in the formula II-3-formyl radical carbazole derivative and the 3-acetocoumarin verivate shown in the formula III with mol ratio 1: (1-1.2) mix, add dissolution with solvents again, add basic catalyst then, reflux 4-6 hour; Product naturally cooling after-filtration is got deposition, will precipitate recrystallization, obtains the 9-ethyl carbazole class chalcone derivative that contains the tonka bean camphor skeleton of formula I;
In formula II and the formula III, R is-NO
2Or-Br, R
1For-H ,-OCH
3,-OH ,-N (CH
2CH
3)
2Or-C (CH
3)
3, R
2=R
3=H or
3. the compound method that contains the 9-ethyl carbazole class chalcone derivative of tonka bean camphor skeleton according to claim 2, it is characterized in that: described solvent is an absolute ethyl alcohol; Or be absolute ethyl alcohol/acetonitrile mixed solvent, wherein the volume of absolute ethyl alcohol and acetonitrile is 2: 1.
4. the compound method that contains the 9-ethyl carbazole class chalcone derivative of tonka bean camphor skeleton according to claim 2, it is characterized in that: described basic catalyst is hexahydropyridine or pyridine.
5. the compound method that contains the 9-ethyl carbazole class chalcone derivative of tonka bean camphor skeleton according to claim 2 is characterized in that: described recrystallization adopts absolute ethyl alcohol-N mixing solutions, and both volumes are 2: 1.
6. the described application of 9-ethyl carbazole class chalcone derivative in luminescent material that contains the tonka bean camphor skeleton of claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012100499646A CN102603720A (en) | 2012-02-29 | 2012-02-29 | 9-ethyl carbazole chalcone derivative containing coumarin skeleton and synthetic method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012100499646A CN102603720A (en) | 2012-02-29 | 2012-02-29 | 9-ethyl carbazole chalcone derivative containing coumarin skeleton and synthetic method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102603720A true CN102603720A (en) | 2012-07-25 |
Family
ID=46521552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2012100499646A Pending CN102603720A (en) | 2012-02-29 | 2012-02-29 | 9-ethyl carbazole chalcone derivative containing coumarin skeleton and synthetic method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102603720A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113024540A (en) * | 2021-03-11 | 2021-06-25 | 中国工程物理研究院激光聚变研究中心 | Preparation method and application of nonlinear compound with D-pi-A structure |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101565378A (en) * | 2009-05-26 | 2009-10-28 | 华中师范大学 | Preparation of derivative of dibenzoyl methane and application thereof |
| CN101565472A (en) * | 2009-05-19 | 2009-10-28 | 常州强力电子新材料有限公司 | Ketoxime ester photoinitiator |
| CN101941939A (en) * | 2010-07-21 | 2011-01-12 | 深圳市有为化学技术有限公司 | Polyfunctional carbazole derivative oxime ester compound and preparation method and light polymerization initiator thereof |
-
2012
- 2012-02-29 CN CN2012100499646A patent/CN102603720A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101565472A (en) * | 2009-05-19 | 2009-10-28 | 常州强力电子新材料有限公司 | Ketoxime ester photoinitiator |
| CN101565378A (en) * | 2009-05-26 | 2009-10-28 | 华中师范大学 | Preparation of derivative of dibenzoyl methane and application thereof |
| CN101941939A (en) * | 2010-07-21 | 2011-01-12 | 深圳市有为化学技术有限公司 | Polyfunctional carbazole derivative oxime ester compound and preparation method and light polymerization initiator thereof |
Non-Patent Citations (2)
| Title |
|---|
| YI-FENG SUN ET AL: "The synthesis, characterization and properties of coumarin-based chromophores containing a chalcone moiety", 《DYES AND PIGMENTS》 * |
| 孙一峰等: "香豆素衍生物的合成及结构表征", 《影像科学与光化学》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113024540A (en) * | 2021-03-11 | 2021-06-25 | 中国工程物理研究院激光聚变研究中心 | Preparation method and application of nonlinear compound with D-pi-A structure |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104530105B (en) | Two boron fluoride complexings two pyrroles's methine derivative organic dyestuff of a kind of diazosulfide or benzene 1,4-Dithiapentalene bridging and preparation method thereof | |
| CN107573928B (en) | A kind of solid-state up-conversion luminescent material and preparation method thereof based on T-T annihilation | |
| Hao et al. | Excited-state intramolecular single and double proton transfer emission of 2, 5-bis (benzoxazol-2-yl) thiophene-3, 4-diol | |
| CN103012174B (en) | Preparation method of water-based fluorescent paint | |
| CN106632239B (en) | A kind of isolonglifolane ketone group hexahydro quinazoline -2- amine schiff's base type fluorescent material and its synthetic method and application | |
| CN106883207A (en) | A kind of preparation method of trimeric indenyl bicoumarin fluorescent dye | |
| CN106189363A (en) | One class closes polymer-metal complex dye sensitizing agent of Cd (II) and its production and use containing 2 (2 ' hydroxy phenyl) benzimidizole derivatives | |
| Manohara et al. | Synthesis, optical and electrochemical properties of new cyanopyridine derivatives | |
| CN107459488B (en) | Isolonglifolane base and pyrimidine -2- amine Schiff bases fluorescent chemicals and preparation method thereof | |
| Qian et al. | Visualized fabric discoloration of bi-heterocyclic hydrazone dyes | |
| Wang et al. | Precise design and synthesis of an AIE fluorophore with near-infrared emission for cellular bioimaging | |
| CN103992271A (en) | Organic fluorescent gel compound based on naphthalimide and preparation method and application thereof | |
| CN105348308B (en) | Bridged bis-boron-dipyrromethene (BODIPY) derivative containing fluorene at meso-position and preparation method thereof | |
| CN103709070A (en) | New organic compound with AIE (aggregation-induced emission) effects and synthesis method thereof | |
| CN104311549B (en) | A kind of synthesis and application of carbazoles dye sensitizing agent | |
| CN104877674A (en) | Aqueous solution capable of generating white fluorescence through excitation and preparation method thereof | |
| CN102491936B (en) | Conjugated compound with yellow-green fluorescence and preparation method and use thereof | |
| CN102516235B (en) | Dibenzothiophene chalcone containing coumarin skeleton and synthesis method and application thereof | |
| CN104311543B (en) | A kind of synthesis and application of the tri-arylamine group dye sensitizing agent containing cumarin | |
| CN105837568B (en) | A kind of fluorenyl β carbolines class compound, its application and preparation method as luminous organic material and aggregation inducing Fluorescence Increasing material | |
| CN105505379A (en) | Long-wavelength BODIPY fluorescent dye derivative and preparation method thereof | |
| CN102603720A (en) | 9-ethyl carbazole chalcone derivative containing coumarin skeleton and synthetic method thereof | |
| CN102702020A (en) | Azo radical-substituted organic small molecular gel, preparation method thereof and application of azo radical-substituted organic small molecular gel to preparation of organic gel | |
| CN110117235A (en) | The compound and its preparation method and application of color shifting properties is caused with aggregation-induced emission and power | |
| CN104387790A (en) | Benzindole salt dye containing thiophene group and preparation method and application of benzindole salt dye |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20120725 |